Water → (3-TERT-BUTOXY-PHENYL)-METHANOL

HRID 1610651Notes

Reaction equation

HRID 1610651 reaction equation
[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=1)[C:9](OCC)=[O:10])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=1)[CH2:9][OH:10])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22261682HCID 22261682, compound

Product 1

HCID 23269370(3-TERT-BUTOXY-PHENYL)-METHANOL

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-tert-butyloxybenzoate (16.7 g, 80 mmol) in tetrahydrofuran (100 ml) was added lithium aluminum hydride (4.55 g, 120 mmol) by small portions under ice-cooling. The mixture was stirred at room temperature for 1 hr. and water (10 ml) was added under ice-cooling to allow decomposition. Insoluble material was filtered off and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1-2:1) to give the objective substance (12.8 g, 88%) as an oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationInsoluble material was filtered off
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1-2:1)
  6. customto give the objective substance (12.8 g, 88%) as an oil

Sources & evidence

ORD record
ord-b1dd10a15552419eb20ef2a9886c4f9e
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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